A bidentate (N- and O-) imine-based ligand(L1)and its metal complexes of types [CuII(L1)2](C1), [CuII(L1)(Phen)](C2), [CoIII(L1)2](C3), and [CoIII(L1)(Phen)](C4)(L1= 2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino)methyl)-4-chlorophenol and phen = 1,10-phenanthroline) were synthesized as potential chemotherapeutic drug candidates. The prepared complexes were structurally characterized by spectral techniques (NMR, FT-IR, LC-MS, EPR, and electronic absorption), thermogravimetric analysis (TGA/DTA), magnetic moment, and CHNO elemental analysis. Spectroscopic studies suggested the distorted octahedral structure for all complexes.In vitrobioassay studies include binding and nuclease activities of the ligand and its complexes with target calf thymus- (CT-) DNA were carried out by employing UV-Vis, fluorescence spectroscopy, viscosity, and gel electrophoresis techniques. The extent of binding propensity was determined quantitatively byKbandKsvvalues which revealed a higher binding affinity for C2and C4as compared to C1and C3. In addition, the scavenging superoxide anion free radical (O∙-2) activity of metal complexes was determined by nitroblue tetrazolium (NBT) light reduction assay. Molecular docking studies with DNA and SOD enzyme were also carried out on these compounds. The antimicrobial study has shown that all the compounds are potential antibacterial agents against Gram-negative bacterial strains and better antifungal agents with respect to standard drugs used.